Oxime chemistry utilizing the highly specific reaction of an aminooxy group to an aldehyde or ketone has been previously established as a possible conjugation scheme. This conjugation scheme has been viewed favorably as the reaction between the aminooxy group and the aldehyde or ketone can occur rapidly and can proceed to high conversion, often without catalysts. In addition, aminooxy reactivity is significantly higher than primary amines, thus conferring the desired specificity for certain types of conjugations. However, one drawback to this approach has generally been the need to engineer the reactants to contain an aldehyde or ketone group and/or an aminooxy group.
Other conventional conjugation methods generally also have drawbacks in that they utilize reaction schemes that involve activating catalysts, include undesirable solvents, require modification of reactants, or necessitate the generation of intermediates. Additionally, conditions (e.g., pH, temperature, reagents) for many typical reactions may cause degradation of the reactants. Furthermore, low reactivity of the molecules or compounds, the addition of reactive groups, and use of unconventional solvents all contribute to complex reaction schemes, low reaction yields, or overall inefficiency.